Hydrochloric Acid → methyl 1-(3-chloropyridin-2-yl)-5-hydroxy-3-(hydroxymethyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

HRID 2044034Notes

Reaction equation

HRID 2044034 reaction equation
[NH2:1][C:2]([CH2:10][OH:11])=[CH:3][C:4](=[O:9])[C:5]([O:7][CH3:8])=[O:6].[Cl:12][C:13]1[C:14]([NH:19]N)=[N:15][CH:16]=[CH:17][CH:18]=1.Cl>C(#N)C>[Cl:12][C:13]1[C:14]([N:19]2[C:4]([OH:9])([C:5]([O:7][CH3:8])=[O:6])[CH2:3][C:2]([CH2:10][OH:11])=[N:1]2)=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5561003-Chloro-2-hydrazinylpyridineHCID 58320700HCID 58320700, compound

Product 1

HCID 54577408methyl 1-(3-chloropyridin-2-yl)-5-hydroxy-3-(hydroxymethyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 4-amino-5-hydroxy-2-oxopent-3-enoate (1.59 g, 10 mmol), 3-chloropyridin-2-ylhydrazine (1.43 g, 10 mmol and HCl (1 g, 10 mmol, 37% solution in water) was stirred in 15 ml of acetonitrile at 25° C. for 20 hours. The solution was concentrated under reduced pressure and the residue was washed with water and isopropanol. This gave 2.13 g (75%) of the product, with a melting point of 111-113° C.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. washthe residue was washed with water and isopropanol

Sources & evidence

ORD record
ord-770042fb5008492a96da17218b5131c0
Source dataset
uspto-grants-2013_11
Patent number
US08586753B2

Reaction notes

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